Hydroxyamine hydrochloride → (S)-4-dibenzofuran-2-yl-4-hydroxyimino-2-(2,2,2-trifluoroacetylamino)-butyric acid

HRID 376407Notes

Reaction equation

[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=O)[CH2:15][C@H:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[C:17]([OH:19])=[O:18].[OH2:28].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:37]O>CO>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[N:37][OH:28])[CH2:15][C@H:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[C:17]([OH:19])=[O:18]

Participants

Conditions

Temperature: 24 °C

Procedure

To a solution of (S)-4-dibenzofuran-2-yl-4-oxo-2,2,2-trifluoroacetylamino)-butyric acid (1.0 g, 0.0026 mol) from Example 1 in 50 mL of methanol was added sodium acetate trihydrate (1.08 g, 0.0079 mol). The solution was stirred at 24° C. while an aqueous solution (5 mL) of hydroxylamine hydrochloride (0.37 g, 0.00527 mol) was added in one portion. The reaction mixture was stirred for 3 hours at 24° C., and then heated to reflux for 2 hours. The solution was cooled to 24° C. and concentrated to dryness by evaporation under reduced pressure. The solid was rinsed with 10 mL of water, and crystallized from ethyl acetate and hexane to afford 0.13 g of (S)-4-dibenzofuran-2-yl-4-hydroxyimino-2-(2,2,2-trifluoroacetylamino)-butyric acid; mp 128-130° C.

Workup

additionwas added in one portion
temperatureheated
temperatureto reflux for 2 hours
temperatureThe solution was cooled to 24° C.
concentrationconcentrated to dryness by evaporation under reduced pressure
washThe solid was rinsed with 10 mL of water
customcrystallized from ethyl acetate and hexane

Sources & evidence

ORD record: ord-3a58cdb5eb524fb881f3b36b228bd0ca
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06020366

Reaction notes

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